Abstract
11-Hydroxy-1,3,5,7,11-pentamethyl-2,4,6,8-tetraoxatricyclo[3.3.3.0(3,7)]undecan-9-one adopts an equilibrium (in CD2CI2 at −90°C) between ca. 68% of the conformer with a pseudo-axial C-11 methyl substituent and ca. 32% of the alternative pseudo-equatorially substituted conformer. The derived cis-9,11-diol, cis-9,11-dimethyldiol and cis-9-phenyl-11-methyldiol adopt conformational equilibria heavily biased towards the diaxial OH conformations which are stabilised by internal H-bonds involving the dioxolan ring oxygen atoms.
Original language | English |
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Pages (from-to) | 10005-10009 |
Number of pages | 5 |
Journal | Tetrahedron Letters |
Volume | 56 |
Issue number | 51 |
DOIs | |
Publication status | Published - 15 Dec 2000 |
Keywords
- stereochemistry
- NMR
- conformation
- butan-2,3-dione tricyclic trimer